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DE69513332D1 - (Thia) cycloalkyl (b) indole derivatives as 5-lipoxygenase inhibitors - Google Patents

(Thia) cycloalkyl (b) indole derivatives as 5-lipoxygenase inhibitors

Info

Publication number
DE69513332D1
DE69513332D1 DE69513332T DE69513332T DE69513332D1 DE 69513332 D1 DE69513332 D1 DE 69513332D1 DE 69513332 T DE69513332 T DE 69513332T DE 69513332 T DE69513332 T DE 69513332T DE 69513332 D1 DE69513332 D1 DE 69513332D1
Authority
DE
Germany
Prior art keywords
alkyl
thia
cycloalkyl
alkoxy
indole derivatives
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Fee Related
Application number
DE69513332T
Other languages
German (de)
Other versions
DE69513332T2 (en
Inventor
Paul Caubere
Brigitte Jamart-Gregoire
Catherine Caubere
Dominique Manechez
Pierre Renard
Gerard Adam
Catherine Nguyen
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
ADIR SARL
Original Assignee
ADIR SARL
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by ADIR SARL filed Critical ADIR SARL
Publication of DE69513332D1 publication Critical patent/DE69513332D1/en
Application granted granted Critical
Publication of DE69513332T2 publication Critical patent/DE69513332T2/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • A61P11/08—Bronchodilators
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P13/00—Drugs for disorders of the urinary system
    • A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P15/00—Drugs for genital or sexual disorders; Contraceptives
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/08—Antiallergic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C07D209/94—[b, c]- or [b, d]-condensed containing carbocyclic rings other than six-membered
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D495/04—Ortho-condensed systems

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Engineering & Computer Science (AREA)
  • Pulmonology (AREA)
  • Urology & Nephrology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Cardiology (AREA)
  • Endocrinology (AREA)
  • Immunology (AREA)
  • Pain & Pain Management (AREA)
  • Rheumatology (AREA)
  • Vascular Medicine (AREA)
  • Reproductive Health (AREA)
  • Dermatology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Indole Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Thiazole And Isothizaole Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)

Abstract

(Thia)cycloalkyl(b)indole derivs. of formula (I), their optical isomers and acid or base addn. salts, are new. R1 = Ar-(CH2)n-O-; n = 0, 1-4; Ar = phenyl, naphthyl, thienyl, furyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiadiazole, oxadiazole, pyridyl, quinolyl, isoquinolyl, indolyl, benzofuryl, or benzothienyl (opt. substd. by one or more halo, alkyl, alkoxy, hydroxy or CF3); R2 = H, halo, alkyl, alkoxy or CF3; R3 = H, alkyl, carboxyalkyl or alkoxycarbonylalkyl; A = -(CH2)m- or a gp. of formula (i); m = 3-6; p = 1-4; alkyl, alkoxy = 1-6C.
DE69513332T 1994-06-28 1995-06-28 (Thia) cycloalkyl (b) indole derivatives as 5-lipoxygenase inhibitors Expired - Fee Related DE69513332T2 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR9407888A FR2721610B1 (en) 1994-06-28 1994-06-28 New (thia) cycloalkyl [b] indole derivatives, process for their preparation and pharmaceutical compositions containing them.

Publications (2)

Publication Number Publication Date
DE69513332D1 true DE69513332D1 (en) 1999-12-23
DE69513332T2 DE69513332T2 (en) 2000-07-27

Family

ID=9464699

Family Applications (1)

Application Number Title Priority Date Filing Date
DE69513332T Expired - Fee Related DE69513332T2 (en) 1994-06-28 1995-06-28 (Thia) cycloalkyl (b) indole derivatives as 5-lipoxygenase inhibitors

Country Status (16)

Country Link
US (1) US5635516A (en)
EP (1) EP0690050B1 (en)
JP (1) JP3004566B2 (en)
CN (1) CN1054374C (en)
AT (1) ATE186722T1 (en)
AU (1) AU686800B2 (en)
CA (1) CA2152725A1 (en)
DE (1) DE69513332T2 (en)
DK (1) DK0690050T3 (en)
ES (1) ES2141904T3 (en)
FI (1) FI953193L (en)
FR (1) FR2721610B1 (en)
GR (1) GR3032172T3 (en)
NO (1) NO305022B1 (en)
NZ (1) NZ272447A (en)
ZA (1) ZA955355B (en)

Families Citing this family (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA2128283A1 (en) * 1993-07-20 1995-01-21 Paul Caubere (thia)cycloalkyl¬b|indoles, their preparation process and pharmaceutical compositions containing them
AU2002322720B2 (en) 2001-07-25 2008-11-13 Raptor Pharmaceutical Inc. Compositions and methods for modulating blood-brain barrier transport
CN103259027A (en) 2005-04-28 2013-08-21 普罗透斯数字保健公司 Pharma-informatics system
US8399666B2 (en) * 2005-11-04 2013-03-19 Panmira Pharmaceuticals, Llc 5-lipoxygenase-activating protein (FLAP) inhibitors
US20070244128A1 (en) * 2005-11-04 2007-10-18 Amira Pharmaceuticals, Inc. 5-lipoxygenase-activating protein (flap) inhibitors
US20070225285A1 (en) * 2005-11-04 2007-09-27 Amira Pharmaceuticals, Inc. 5-lipoxygenase-activating protein (flap) inhibitors
US20070219206A1 (en) * 2005-11-04 2007-09-20 Amira Pharmaceuticals, Inc. 5-lipoxygenase-activating protein (flap) inhibitors
GB2431927B (en) * 2005-11-04 2010-03-17 Amira Pharmaceuticals Inc 5-Lipoxygenase-activating protein (FLAP) inhibitors
US7977359B2 (en) 2005-11-04 2011-07-12 Amira Pharmaceuticals, Inc. 5-lipdxygenase-activating protein (FLAP) inhibitors
EP2063905B1 (en) 2006-09-18 2014-07-30 Raptor Pharmaceutical Inc Treatment of liver disorders by administration of receptor-associated protein (rap)-conjugates
US7925075B2 (en) * 2007-05-07 2011-04-12 General Electric Company Inspection system and methods with autocompensation for edge break gauging orientation
TW200920369A (en) * 2007-10-26 2009-05-16 Amira Pharmaceuticals Inc 5-lipoxygenase activating protein (flap) inhibitor
EA019819B1 (en) * 2008-05-23 2014-06-30 ПАНМИРА ФАРМАСЬЮТИКАЛЗ, ЭлЭлСи C crystalline polymorphic form of protein inhibitor activating 5-lipoxygenase, pharmaceutical composition based thereon and use in treatment
US8546431B2 (en) 2008-10-01 2013-10-01 Panmira Pharmaceuticals, Llc 5-lipoxygenase-activating protein (FLAP) inhibitors
CN102316902B (en) 2009-02-20 2014-09-24 to-BBB控股股份有限公司 Glutathione-based drug delivery system
CN110075069A (en) 2009-05-06 2019-08-02 实验室护肤股份有限公司 Include activating agent-calcium phosphate granules compound dermal delivery composition and its application
US20120077778A1 (en) 2010-09-29 2012-03-29 Andrea Bourdelais Ladder-Frame Polyether Conjugates
US11633379B2 (en) 2017-01-04 2023-04-25 Trustees Of Dartmouth College Methods of inhibiting PCSK9
CN108558905B (en) * 2018-05-21 2021-03-12 华南农业大学 Thiopyran [4,3-b ] indole compound and preparation method and application thereof

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2243574A1 (en) 1972-09-05 1974-03-14 Boehringer Mannheim Gmbh Carbazolyl- and phenothiazinyl oxy acetic acid derivs - against coronary diseases and atherosclerosis from corresp. heterocyclic hydroxy-cpds. and halo acetic esters
GB1432649A (en) * 1973-09-07 1976-04-22 Ici Ltd
CA1326030C (en) * 1987-07-21 1994-01-11 John W. Gillard Cyclohept[b]indolealkanoic acids
PT95692A (en) * 1989-10-27 1991-09-13 American Home Prod PROCESS FOR THE PREPARATION OF INDOLE-, INDENO-, PYRANOINDOLE- AND TETRA-HYDROCARBAZOLE-ALCANOIC ACID DERIVATIVES, OR WHICH ARE USEFUL AS PLA2 INHIBITORS AND LIPOXIGENASE
US5221678A (en) * 1990-07-26 1993-06-22 Merck Frosst Canada, Inc. (quinolin-2-ylmethoxy)tetrahydrocarbazoles as inhibitors of the biosynthesis of leukotrienes
AU3128693A (en) * 1991-11-18 1993-06-15 G.D. Searle & Co. 2-(4-substituted)phenylmethylene derivatives and methods of use
US5288751A (en) * 1992-11-06 1994-02-22 Abbott Laboratories [(Substituted) phenyalkyl]furylalkynyl-and [substituted) phenyalkyl] thienylalkynyl-N-hydroxyurea inhibitors or leukotriene biosynthesis
US5314900A (en) * 1992-11-19 1994-05-24 Merck Frosst Canada, Inc. Aryl thiopyrano[2,3,4-C,D]indoles as inhibitors of leukotriene biosynthesis
ES2062943B1 (en) * 1993-03-23 1995-11-16 Uriach & Cia Sa J NEW DERIVATIVES OF (2-METHYL-3-PIRIDIL) CYANOMETILPIPERAZINES.
CA2128283A1 (en) * 1993-07-20 1995-01-21 Paul Caubere (thia)cycloalkyl¬b|indoles, their preparation process and pharmaceutical compositions containing them

Also Published As

Publication number Publication date
NO305022B1 (en) 1999-03-22
NZ272447A (en) 1996-02-27
AU686800B2 (en) 1998-02-12
CN1054374C (en) 2000-07-12
AU2327495A (en) 1996-01-11
DK0690050T3 (en) 2000-04-17
EP0690050B1 (en) 1999-11-17
JPH0812649A (en) 1996-01-16
JP3004566B2 (en) 2000-01-31
FI953193A0 (en) 1995-06-28
FR2721610B1 (en) 1996-08-23
NO952579L (en) 1995-12-29
FR2721610A1 (en) 1995-12-29
ATE186722T1 (en) 1999-12-15
US5635516A (en) 1997-06-03
NO952579D0 (en) 1995-06-27
CA2152725A1 (en) 1995-12-29
ZA955355B (en) 1996-02-12
FI953193L (en) 1995-12-29
DE69513332T2 (en) 2000-07-27
CN1114957A (en) 1996-01-17
EP0690050A1 (en) 1996-01-03
GR3032172T3 (en) 2000-04-27
ES2141904T3 (en) 2000-04-01

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Legal Events

Date Code Title Description
8364 No opposition during term of opposition
8339 Ceased/non-payment of the annual fee